In early 2023, I faced a professionally driven existential crisis. Not the typical 'Is this worth it?' but the more unsettling question: 'Am I still worthy of this?' Leading a team in a hyper-growth organization as CTO (we had nearly 100% compounded annual growth since COVID) had its inevitable challenges. Missed deadlines, software bugs, and fast-changing demands became my burden—not because they were thrust upon me, but because I believed in extreme ownership as a core leadership principle. This philosophy of taking ultimate responsibility meant that every setback became more than just a problem to solve; it became a weight I carried, a reflection of my perceived inadequacies.

This is the hidden tax of leadership. I've come to think of the weight of perceived failures and relentless expectations as 'Battered Executive Syndrome.' It's not unique to me, but it’s rarely discussed. Many of us, especially those deeply invested in our work, wrestle with self-doubt. It’s as if imposter syndrome is always whispering at the edges of our accomplishments, quietly magnifying every critique or subtle signal into a reflection of our inadequacies. I took every failure far too seriously at the time as if one misstep could rewrite my entire story. Oh, the stories I began to tell myself - “Maybe I’m not a leader that can Get Shit Done. Maybe I’m not as functional as I thought I was as a CTO.” I became a reflection of my failures without learning lessons from them, and being a highly competitive person who is wired to WIN, it began eating at me.

Start Again

So, I began planning my exit. I laid out a succession plan, carefully transitioned my role, and started building something new that felt both intellectually challenging and creatively fulfilling. I wanted to be able to more easily control the ground rules and what "success" looked like. Akin to David Goggins going from Navy Seal to Army Ranger to Wildland Firefighter or Sam Harris resetting his focus in meditation, I embraced the power of starting again. I launched a quantitative finance business focusing on wealth preservation, and have spent thousands of hours creating a systematic trading platform from scratch. In many ways, I was shedding a skin, that shadow that had been following me, not to leave something behind but to uncover something new. Each setback and restart became an opportunity to recommit, refine, and evolve. This perpetual return to the challenge embodied true resilience. Yet I didn't realize that true transformation would come not from escaping my challenges but from embracing an entirely new one.

Leaping into the Unknown

Then, one day, opportunity called. A friend and former colleague reached out with a proposition. "We have a client that needs your help," he said. "They need you." I’ve always said “yes” to new opportunities, even when it means diving headfirst into uncharted waters. My path is littered with examples: moving to Germany to implement software I’d never logged into, taking a job as a mid-level software developer having never written any production code, and taking over a department having never managed someone. It’s a tendency that occasionally gets me into trouble and has led to some of my greatest successes and evolutions. I had to leap into the unknown, knowing the net might not appear. That “yes” turned out to be life-changing.

As I stepped into the fray, the problem was familiar, though the industry wasn't. A near-centenarian business had started down the audacious road of digitizing its operations but was challenged by a new paradigm - proprietary software. Despite their deep experience, they showed remarkable humility in vocalizing their need for help. Here I was, still wrestling with my self-doubt, yet faced with an opportunity that seemed to mirror my journey: a successful organization willing to acknowledge its vulnerabilities and start fresh. My insecure monkey brain battled the urge to take on this challenge, but something about their openness to change resonated deeply with my experience.

I discovered something transformative about leadership, growth, and two big lessons through this unexpected turn.

Lesson 1: On Humility…

One of the most important revelations for me was that I had to do something I hadn't done in nearly a decade: earn trust from the ground up. Before this, I'd spent years with the same executive team, each relationship built on battles fought together. I didn't have much to prove to stay there, and that was likely what made the trounces of failure slap me in the face even more. I would say to myself, "How could this be? Look at what I've built!"

Now, I was back at the starting line, with new doubts but a different team. I had to remember, redefine, and reimagine what made me trustworthy. The path forward demanded a new operating system built on the delicate balance between hubris and humility. It meant having the confidence to say, "I am good at this, and it is my craft," while embracing the humility to admit, "I don't know anything and am just making it up as I go." This wasn't about choosing between expertise and uncertainty but finding strength in their coexistence. To say, 'I am good at this,' and then in the same breath admit, 'I'm also figuring this out as I go,' became the essential dichotomy of authentic leadership.

Lesson 2: Winning Together

I also found myself on the ultimate team. They weren't operating internally with an “us-versus-them” mentality but instead with a unified front driven by a desire to win. What I experienced went more profound than just doing a good job daily. This was a team that showed true partnership—a team all striving for the same outcome. Sure, there was sometimes frustration, but that's almost a given when the goals are big and ambitious, and the people are winners. What struck me was that this team was operating as a team, where every position felt wanted and needed. Winning wasn't about individual survival; it was a shared mission, a victory we could all claim.

Only in hindsight can I reconcile how my previous environment had strayed from this path. A subtle culture of "shifting pressure from team to team" had emerged, keeping the flywheel spinning but ultimately leading to finger-pointing and hunting internal ghosts whenever progress stalled. While our previous success might have been impressive—near 100% growth year over year—looking back, I can't help but think those wins were more a product of market momentum than true cohesion. We were so busy finding the pariah that we forgot the fundamental truth: true success isn't about passing the load; it's about lifting it together.

Fail to WIN

Self-doubt is far more common among leaders than most admit. That "Battered Executive Syndrome" I experienced—the weight of perceived failures and relentless expectations—is a universal step in everyone’s leadership journey. Like learning to walk, leadership is a series of stumbles and falls, where the weight of our perceived failures often comes from taking ourselves—and these inevitable stumbles—too seriously. As seriousness takes hold, the stories we tell ourselves stray from the Truth, becoming shadows of insecurity that let demons take hold.

In a recent interview with Lance Armstrong, Kimbal Musk shared advice from his brother to "fail fast and use that feedback to grow iteratively." This principle mirrors the fundamental nature of growth: just as a child learns to walk through countless falls, each providing vital feedback about balance and momentum, leaders grow through cycles of failure and adaptation. What feels like proof of inadequacy at the moment reveals itself over time as a necessary step toward mastery—each stumble teaching us to balance hubris with humility and individual achievement with team success.

Leadership isn't about achieving perfect balance on the first try—it's about embracing the wobbles and falls along the way. The path forward requires the humility to accept help when stumbling and the wisdom to lift others when they fall. Growth happens when you let go of the need for perfection, finding strength in the vulnerability of learning alongside your team. Not taking yourself—or your failures—too seriously becomes the key to staying in the game.

Finding one's vocation requires this continuous cycle of falling and rising, each experience demanding that delicate balance between confidence and humility, individual drive and team cohesion. It requires finding people who understand that winning means everyone crosses the finish line together. The key lies not in avoiding falls but in how you handle them: own them, inspect them, and accept them as part of the process. Only then can you transform these stumbles from perceived failures into the steps that move you and your team forward.

Durability and endurance, in my estimation, are some of the most essential qualities of leadership. They’re traits so ingrained in high performers that they often are fetishized in the grind culture. But when I sat down with my executive coach last week, the conversation turned toward an uncomfortable truth: durability can be a double-edged sword. I was sharing the usual dynamics — struggles with balancing time, managing the whirlwind of priorities, and the stress that was compounding from not being able to do either well. At times, my reaction to something trivial spiraled out of control. Her response was simple but pointed: “If you can’t show up at 100% for yourself, you won’t be able to do it for your people or your business either.” It was a powerful reminder that if it’s all grind all the time, your best work won’t come through.

Leadership, in a sense, can be lonely. There’s a proverb: “The higher the monkey climbs, the more he shows his ass.” It’s easy to spin stories in our heads about what it takes to operate, how much we should be working, what’s truly necessary. But unchecked, that can often lead us down the wrong path and narrative we tell ourselves. My recent conversation with my coach cut through those stories. Here I was, pushing through every day, expecting that if I just kept grinding, I’d somehow sustain everything—my work, my team, my vision. But that’s not how it works. In leadership, durability and endurance are not quite the same thing, and this difference is significant.

Durability is the ability to resist wear and tear—to keep going in the face of constant challenges without breaking down. It’s like armor: it deflects damage. But armor alone isn’t enough. Endurance is different; it’s about how much you can take before needing rest, about having the resilience to bounce back and keep moving forward. Endurance is more than just “grinding it out”—it requires pacing, recovery, and sometimes, stopping entirely. It’s what allows you to sustain that push over time. Not every day will be good. Problems will come at you from all angles, and you’re expected to solve them—whether they’re people problems, business problems, or personal ones. But if problem-solving becomes synonymous with constant suffering, you’re no longer just enduring; you’re stuck.

Those who know me well know I’m an avid cyclist, having spent much of my early adulthood training and racing bikes in all disciplines. As an athlete, I learned the value of both durability and endurance firsthand. When you’re training and racing at a high level, you get used to discomfort, and you must keep pushing through. You must endure. Grit, resilience, the ability to get comfortable with being uncomfortable—all of these unlock true potential. But you also learn that peak performance requires more than just grinding every day; it requires rest, preparation, and pacing. You can’t race at your best without time to recover. A bad race, a minor injury, or a sub-par training ride isn’t a reason to quit. But when these things become systemic, it’s time to pause and re-evaluate.

There’s a common saying that “the definition of insanity is doing the same thing over and over and expecting different results.” When discomfort becomes a permanent state in your work, you have to step back and reconsider. Maybe it’s not about grit or resilience anymore. Maybe it’s about rethinking your approach entirely.

This is where many high performers—myself included—struggle. We pride ourselves on perseverance, on getting things done, on pushing through. But what if the very thing we need to do is stop? What if true durability in leadership is about recognizing when to not push forward? To pause, to think, to reset.

Andy Grove, in High Output Management, talks about the role of leaders as firefighters, constantly putting out flames. But there’s a point where firefighting turns into a never-ending cycle of chaos. The real challenge isn’t just fighting fires—it’s knowing when to create a firebreak. It’s the moment when you clear your calendar, step back, and make space for real thinking. First principles thinking. Root cause analysis. That’s where breakthroughs come from, not from pushing harder but from stopping and reflecting.

This idea of a firebreak isn’t just theoretical. I’ve seen firsthand how stepping back to solve a recurring issue can unlock new possibilities. One recent experience involved a chaotic project with endless setbacks. Instead of powering through and piling on more work, I created a firebreak—took a step back, paused all action, and focused only on the root cause. Within a short, concentrated amount of time, I identified the core problem and got the team back on track. The solution wasn’t in more effort; it was in creating the space to understand. Interestingly, I’ve had this level of insight come from things like family vacations or even just walking or working out in silence.

It’s not just about creating space to solve problems. You also need to carve out time for creativity. Often, productivity and the relentless drive to "get shit done" (GSD) can stifle the very creativity we need to solve the toughest problems. There’s something powerful about stepping away from the grind—whether it’s going for a walk, sitting in silence, or even daydreaming—and allowing your mind to wander. That’s when the simple solution to a complex problem tends to appear. It’s as though our brains work better in the background, freed from the constraints of productivity. We often solve our biggest problems when we aren’t actively trying to solve them.

Productivity can be the enemy of creativity. When you’re always focused on efficiency and output, you lose the space for those creative breakthroughs. This is why it’s essential to bake in moments of disconnect, not just to recharge, but to let your mind roam freely. These are the moments when you get inspired, when an elusive idea finally clicks into place. It’s in that daydream-like state, when you’re not actively trying to GSD, that you often unlock the best solutions.

Installing this skill—the ability to balance durability with strategic withdrawal and creativity—is critical. It’s not about giving up or slowing down; it’s about recognizing when the path you’re on isn’t leading anywhere new. This is not something you can template or schedule. It’s personal. Everyone has their own breaking point, and recognizing yours is one of the most valuable leadership tools you can have.

Failing to do so leads to bad decisions, compounding issues, and a lack of focus on what really matters. When you’re operating at less than 100%, you’re not only failing yourself—you’re failing everything of value around you. The irony of durability is that it’s not about always enduring. True durability isn’t just resistance; it’s knowing when to let go so you can endure even longer.